5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5H-furan-2-one

ID: ALA2115433

Cas Number: 860649-42-9

PubChem CID: 54676508

Max Phase: Preclinical

Molecular Formula: C9H12O6

Molecular Weight: 216.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OCC(C2OC(=O)C(O)=C2O)O1

Standard InChI:  InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3

Standard InChI Key:  POXUQBFHDHCZAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    5.2010   -4.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3868   -4.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -4.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8646   -3.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -3.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032   -2.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848   -2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730   -3.7803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2977   -3.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6123   -5.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9673   -5.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4872   -2.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  6  1  0
  8  7  1  0
  9 10  1  0
 10  6  1  0
 11  4  2  0
 12  1  1  0
 13  2  1  0
 14  8  1  0
 15  8  1  0
  5  3  1  0
  8  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115433

   5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 216.19

Molecular Weight (Monoisotopic): 216.0634

AlogP: 0.39

#Rotatable Bonds: 1

Polar Surface Area: 85.22

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.52

CX Basic pKa: ┄

CX LogP: -0.21

CX LogD: -3.00

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.62

Np Likeness Score: 1.85

References

1. Abell AD, Ratcliffe MJ, Gerrard J..  (1998)  Ascorbic acid-based inhibitors of alpha-amylases.,  8  (13): [PMID:9873419] [10.1016/s0960-894x(98)00298-4]

2. Abell AD, Ratcliffe MJ, Gerrard J..  (1998)  Ascorbic acid-based inhibitors of alpha-amylases.,  8  (13): [PMID:9873419] [10.1016/s0960-894x(98)00298-4]

3. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

• Scientific Literature